Browsing by Author "Soto-Delgado, Jorge"

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    Combined molecular modelling and 3D-QSAR study for understanding the inhibition of NQO1 by heterocyclic quinone derivatives
    (2018) Lopez-Lira, Claudia; Alzate-Morales, Jans H.; Paulino, Margot; Mella-Raipan, Jaime; Salas, Cristian O.; Tapia Apati, Ricardo; Soto-Delgado, Jorge
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    New benzimidazolequinones as trypanosomicidal agents
    (2021) Lopez-Lira, Claudia; Tapia, Ricardo A.; Herrera, Alejandra; Lapier, Michel; Maya, Juan D.; Soto-Delgado, Jorge; Oliver, Allen G.; Lappin, A. Graham; Uriarte, Eugenio
    Herein, the design and synthesis of new 2-phenyl(pyridinyl)benzimidazolequinones and their 5-phenoxy derivatives as potential anti-Trypanosoma cruzi agents are described. The compounds were evaluated in vitro against the epimastigotes and trypomastigote forms of Trypanosoma cruzi. The replacing of a benzene moiety in the naphthoquinone system by an imidazole enhanced the trypanosomicidal activity against Trypanosoma cruzi. Three of the tested compounds (11a-c) showed potent trypanosomicidal activity and compound 11a, with IC50 of 0.65 mu M on the trypomastigote form of T. cruzi, proved to be 15 times more active than nifurtimox. Additionally, molecular docking studies indicate that the quinone derivatives 11a-c could have a multitarget profile interacting preferentially with trypanothione reductase and Old Yellow Enzyme.
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    On the mechanism of biological activity of hydroquinone derivatives that inhibit tumor cell respiration. A theoretical study
    (2013) Soto-Delgado, Jorge; Bahamonde-Padilla, Victor; Araya-Maturana, Ramiro; Weiss-Lopez, Boris E.
    A simple mechanism to understand the biological activity of a series of hydroquinone derivatives is proposed. To validate this proposition Gibbs free energies of formation of the different species involved were calculated. The calculations were performed using density functional theory (DFT) at B3LYP/6-31++G(2df,p) level of theory, including solvation effect. The results show that two important variables to examine are the equilibrium phenol-phenoxide and the solvation energy of neutral species, since the balance between both variables affects the capability of the molecules to cross membranes. Once the molecule crossed the membrane, the formation of radical species shows a qualitative correlation with the magnitude of IC50 values. This provides a reasonable criterion to search for more efficient anticancer drug. (C) 2013 Elsevier B.V. All rights reserved.